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In the off-season of 1985, Mike Illitch opened his wallet and spent freely on several college free agents. Illitch and Detroit general manager Jimmy Devellano were hoping to hit a home run by finding a diamond in the undrafted rough. It's always a long shot, but once in a while it actually works.

The Red Wings did well in signing Adam Oates out of Rensselaer Polytechnic Institute. He became one of the top players of the 1990s and a Hockey Hall of Famer. The only problem was the Red Wings traded him off before he really emerged as a star.

The rest of the Wings gambles did not work out. At all.

The other free agents signed were Ray Staszak (with great fanfare and a big contract), Dale Krentz, Chris Cichocki, and an undersized defenseman from Burbank, California named Tim Friday.

He played with Oates at RPI, helping the school win the NCAA Division 1 championship in 1985. But Friday was in over his head at the NHL level.

A NHL defenseman can not afford to be both slow-footed and not physical. Friday also could not adjust to much faster pace of play. He handled the puck like it was a grenade. He played as if he wanted no piece of that puck.

Friday's NHL career lasted just 23 games. He would suffer a shoulder injury against Philadelphia in December of 1985. He did return to the ice, mostly in the minor leagues where he put up solid numbers at the AHL level. He even helped Adirondack capture the Calder Cup championship.

But the injury ultimately ended Friday's hockey career. He was playing in the AHL while still struggling with the shoulder injury. Not willing to risk further injury, Friday decided to retire on a strong note after winning the AHL title.

According to Wikipedia Tim Friday now lives in Framingham, Massachusetts and owns Water Street Wine and Spirits.